Water → 1,1-Dimethylethyl N-[3-methyl-1-(phenylmethyl)-3-pyrrolidinyl]carbamate

HRID 69498Notes

Reaction equation

HRID 69498 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH3:16])(C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.O.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:22](=[O:31])[NH:19][C:10]1([CH3:16])[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 36840571-Benzyl-3-methylpyrrolidine-3-carboxylic acid

Product 1

HCID 104937341,1-Dimethylethyl N-[3-methyl-1-(phenylmethyl)-3-pyrrolidinyl]carbamate

Procedure

A solution of 1-benzyl-3-methyl-pyrrolidine-3-carboxylic acid (500 mg), triethylamine (231 mg) and diphenylphosphoryl azide (640 mg) in tert-butanol (15 mL) was stirred at 95° C. for 4 h. After adding water it was extracted with dichloromethane, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. In this way the product was obtained with molecular weight 290.41 (C17H26N2O2); MS (ESI): 291 (M+H+).

Workup

  1. extractionwas extracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel
  5. customIn this way the product was obtained with molecular weight 290.41 (C17H26N2O2)

Sources & evidence

ORD record
ord-b7b576ecc6d64312ac4a75c1fbd3111d
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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